Ring-Expansion Reaction of Oximes with Aluminum Reductants

The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl(2), AlH(3) (alane), LiAlH(4), LiAlH(O(t)Bu)(3), and (MeOCH(2)CH(2)O)(2)AlH(2)Na (Red-Al) were examined. Among reductants, AlHCl(2) (LiAlH(4):AlCl(3) = 1:3) in cyclopentyl methyl eth...

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Detalles Bibliográficos
Autores principales: Cho, Hidetsura, Iwama, Yusuke, Mitsuhashi, Nakako, Sugimoto, Kenji, Okano, Kentaro, Tokuyama, Hidetoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268446/
https://www.ncbi.nlm.nih.gov/pubmed/22699568
http://dx.doi.org/10.3390/molecules17067348
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author Cho, Hidetsura
Iwama, Yusuke
Mitsuhashi, Nakako
Sugimoto, Kenji
Okano, Kentaro
Tokuyama, Hidetoshi
author_facet Cho, Hidetsura
Iwama, Yusuke
Mitsuhashi, Nakako
Sugimoto, Kenji
Okano, Kentaro
Tokuyama, Hidetoshi
author_sort Cho, Hidetsura
collection PubMed
description The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl(2), AlH(3) (alane), LiAlH(4), LiAlH(O(t)Bu)(3), and (MeOCH(2)CH(2)O)(2)AlH(2)Na (Red-Al) were examined. Among reductants, AlHCl(2) (LiAlH(4):AlCl(3) = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.
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spelling pubmed-62684462018-12-12 Ring-Expansion Reaction of Oximes with Aluminum Reductants Cho, Hidetsura Iwama, Yusuke Mitsuhashi, Nakako Sugimoto, Kenji Okano, Kentaro Tokuyama, Hidetoshi Molecules Article The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl(2), AlH(3) (alane), LiAlH(4), LiAlH(O(t)Bu)(3), and (MeOCH(2)CH(2)O)(2)AlH(2)Na (Red-Al) were examined. Among reductants, AlHCl(2) (LiAlH(4):AlCl(3) = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields. MDPI 2012-06-14 /pmc/articles/PMC6268446/ /pubmed/22699568 http://dx.doi.org/10.3390/molecules17067348 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Cho, Hidetsura
Iwama, Yusuke
Mitsuhashi, Nakako
Sugimoto, Kenji
Okano, Kentaro
Tokuyama, Hidetoshi
Ring-Expansion Reaction of Oximes with Aluminum Reductants
title Ring-Expansion Reaction of Oximes with Aluminum Reductants
title_full Ring-Expansion Reaction of Oximes with Aluminum Reductants
title_fullStr Ring-Expansion Reaction of Oximes with Aluminum Reductants
title_full_unstemmed Ring-Expansion Reaction of Oximes with Aluminum Reductants
title_short Ring-Expansion Reaction of Oximes with Aluminum Reductants
title_sort ring-expansion reaction of oximes with aluminum reductants
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268446/
https://www.ncbi.nlm.nih.gov/pubmed/22699568
http://dx.doi.org/10.3390/molecules17067348
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AT sugimotokenji ringexpansionreactionofoximeswithaluminumreductants
AT okanokentaro ringexpansionreactionofoximeswithaluminumreductants
AT tokuyamahidetoshi ringexpansionreactionofoximeswithaluminumreductants

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